The enantioselective synthesis of 1-(R)-hydroxypolygodial and its epimer at C-9 is described. alfa-Ionone was the starting material. Key steps of these syntheses included a Corey–Bakshi–Shibata oxazaborolidine-mediated reduction and a stereoselective Diels–Alder reaction. No vanilloid activity was detected for both compounds in assays on VR1 vanilloid receptor in HEK cells transfected with the human VR1.
Enantioselective Synthesis of 1 (R)-hydroxypolygodial and its 9a epimer, 1-(R)-hydroxyisotadeonal
DELLA MONICA, Carmela;DELLA SALA, Giorgio;IZZO, Irene;SPINELLA, Aldo
2007
Abstract
The enantioselective synthesis of 1-(R)-hydroxypolygodial and its epimer at C-9 is described. alfa-Ionone was the starting material. Key steps of these syntheses included a Corey–Bakshi–Shibata oxazaborolidine-mediated reduction and a stereoselective Diels–Alder reaction. No vanilloid activity was detected for both compounds in assays on VR1 vanilloid receptor in HEK cells transfected with the human VR1.File in questo prodotto:
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